A flying bird.
No, that's a person. The correct shape is a bird.
An odd, irregular blob shape with a short handle on the left.
No, not that one. This shape has a short, blunt handle on the left, a large blob on the right.
Correct. A goblet or chalice.
No, not that one. This shape has a wide top, narrow middle, and wide base.
A gem set into a tall stand.

Outcome: successful
Speaker comments: Some right choices on wrong descriptions by the bot, but we got there in the end. :)